Ammonia → 1-(3-Fluorophenyl)-3,4-dihydroisoquinoline

HRID 2383032

Reaction equation

HRID 2383032 reaction equation
P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[C:24]([NH:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O.N>O>[F:20][C:21]1[CH:22]=[C:23]([C:24]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][N:26]=2)[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 7627373-fluoro-N-(2-phenylethyl)benzamide

Product 1

HCID 149989031-(3-Fluorophenyl)-3,4-dihydroisoquinolineYield 105.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Phosphoric acid (11.9 mL) was added to diphosphorus pentoxide (20.0 g) over 5 minutes. The mixture was stirred at 150° C. for 0.5 hours. 3-fluoro-N-(2-phenylethyl)benzamide (5.00 g) was added to the mixture, followed by stirring at 160° C. for 2.5 hours. After cooling, water was added to the reaction solution to which 28% aqueous ammonia was then added to be alkaline. The reaction solution was extracted with EtOAc, washed with saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 1-(3-fluorophenyl)-3,4-dihydroisoquinoline (4.87 g).

Workup

  1. stirringby stirring at 160° C. for 2.5 hours
  2. temperatureAfter cooling
  3. additionwas then added
  4. extractionThe reaction solution was extracted with EtOAc
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e322bbcebb1e4c079f7ceffd64ce5c5e
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Linked notes

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